Rhodium(II)-catalyzed cyclization of bis(N-tosylhydrazone)s: An efficient approach towards polycyclic aromatic compounds

Angewandte Chemie - International Edition

Volumn 51, Issue 23, 2012, Pages 5714-5717

  Xia, Ying ^a   Liu, Zhenxing ^a   Xiao, Qing ^a   Qu, Peiyuan ^a   Ge, Rui ^a   Zhang, Yan ^a   Wang, Jianbo ^a,b  

^a PEKING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

carbenes; cyclizations; diazo compounds; hydrazones; synthetic methods

Indexed keywords

CARBENES; CYCLIZATIONS; DIAZO COMPOUNDS; HYDRAZONES; SYNTHETIC METHODS;

AROMATIC COMPOUNDS; CATALYSIS; REACTION INTERMEDIATES; RHODIUM;

CYCLIZATION;

AZO COMPOUND; CARBENE; DRUG DERIVATIVE; HYDRAZONE DERIVATIVE; METHANE; POLYCYCLIC HYDROCARBON; RHODIUM;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION;

AZO COMPOUNDS; CATALYSIS; CYCLIZATION; HYDRAZONES; METHANE; POLYCYCLIC COMPOUNDS; RHODIUM;

EID: 84861594718     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201201374     Document Type: Article

References (79)

1. R. G. Harvey, Polycyclic Aromatic Hydrocarbons, Wiley-VCH, New York, 1997.
2. A. J. Floyd, S. F. Dyke, S. E. Ward, Chem. Rev. 1976, 76, 509
3. C. B. de Koning, A. L. Rousseau, W. A. L. van Otterlo, Tetrahedron 2003, 59, 7
4. R. G. Harvey, Curr. Org. Chem. 2004, 8, 303
5. S. Kotha, S. Misra, S. Halder, Tetrahedron 2008, 64, 10775.
6. F. Dubois, M. Gingras, Tetrahedron Lett. 1998, 39, 5039
7. A.-E. Gies, M. Pfeffer, J. Org. Chem. 1999, 64, 3650
8. A. Iuliano, P. Piccioli, D. Fabbri, Org. Lett. 2004, 6, 3711
9. S. Some, B. Dutta, J. K. Ray, Tetrahedron Lett. 2006, 47, 1221
10. Y. H. Kim, H. Lee, Y. J. Kim, B. T. Kim, J.-N. Heo, J. Org. Chem. 2008, 73, 495
11. V. Mamane, F. Louërat, J. Iehl, M. Abboud, Y. Fort, Tetrahedron 2008, 64, 10699
12. F. Ye, Y. Shi, L. Zhou, Q. Xiao, Y. Zhang, J. Wang, Org. Lett. 2011, 13, 5020.
13. J. E. McMurry, Acc. Chem. Res. 1983, 16, 405
14. B. E. Kahn, R. D. Rieke, Chem. Rev. 1988, 88, 733
15. J. E. McMurry, Chem. Rev. 1989, 89, 1513.
16. R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413
17. A. Fürstner, Angew. Chem. 2000, 112, 3140
18. Angew. Chem. Int. Ed. 2000, 39, 3012
19. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18
20. Handbook of Metathesis (Ed.:, R. H. Grubbs,), Wiley-VCH, Weinheim, 2003
21. T. J. Donohoe, A. J. Orr, M. Bingham, Angew. Chem. 2006, 118, 2730
22. Angew. Chem. Int. Ed. 2006, 45, 2664
23. S. Kotha, K. Mandal, Chem. Asian J. 2009, 4, 354
24. W. A. L. van Otterlo, C. B. de Koning, Chem. Rev. 2009, 109, 3743.
25. K.-S. Huang, E.-C. Wang, Tetrahedron Lett. 2001, 42, 6155
26. H. Sakurai, T. Daiko, T. Hirao, Science 2003, 301, 1878
27. M. C. Bonifacio, C. R. Robertson, J.-Y. Jung, B. T. King, J. Org. Chem. 2005, 70, 8522
28. V. Mamane, Y. Fort, J. Org. Chem. 2005, 70, 8220
29. S. C. Pelly, C. J. Parkinson, W. A. L. van Otterlo, C. B. de Koning, J. Org. Chem. 2005, 70, 10474
30. K. Yoshida, T. Imamoto, J. Am. Chem. Soc. 2005, 127, 10470
31. S. K. Collins, A. Grandbois, M. P. Vachon, J. Côté, Angew. Chem. 2006, 118, 2989
32. Angew. Chem. Int. Ed. 2006, 45, 2923
33. K. Yoshida, H. Takahashi, T. Imamoto, Chem. Eur. J. 2008, 14, 8246
34. K. Yoshida, R. Narui, T. Imamoto, Chem. Eur. J. 2008, 14, 9706
35. S. Higashibayashi, H. Sakurai, J. Am. Chem. Soc. 2008, 130, 8592
36. A. Grandbois, S. K. Collins, Chem. Eur. J. 2008, 14, 9323
37. K. Yoshida, F. Kawagoe, K. Hayashi, S. Horiuchi, T. Imamoto, A. Yanagisawa, Org. Lett. 2009, 11, 515
38. K. Yoshida, K. Hayashi, A. Yanagisawa, Org. Lett. 2011, 13, 4762.
39. T. Ye, M. A. McKervey, Chem. Rev. 1994, 94, 1091
40. A. Padwa, D. J. Austin, Angew. Chem. 1994, 106, 1881
41. Angew. Chem. Int. Ed. Engl. 1994, 33, 1797
42. A. Padwa, M. D. Weingarten, Chem. Rev. 1996, 96, 223
43. M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, Wiley, New York, 1998
44. M. P. Doyle, D. C. Forbes, Chem. Rev. 1998, 98, 911
45. Z. Zhang, J. Wang, Tetrahedron 2008, 64, 6577.
46. C. Grundmann, Justus Liebigs Ann. Chem. 1938, 536, 29.
47. W. Baratta, A. Del Zotto, P. Rigo, Chem. Commun. 1997, 2163
48. M. P. Doyle, M. Yan, J. Org. Chem. 2002, 67, 602
49. D. M. Hodgson, D. Angrish, Chem. Commun. 2005, 4902
50. D. M. Hodgson, D. Angrish, Chem. Eur. J. 2007, 13, 3470
51. J. H. Hansen, B. T. Parr, P. Pelphrey, Q. Jin, J. Autschbach, H. M. L. Davies, Angew. Chem. 2011, 123, 2592
52. Angew. Chem. Int. Ed. 2011, 50, 2544.
53. J. Font, F. Serratosa, J. Valls, Chem. Commun. 1970, 721
54. S. Kulkowit, M. A. McKervey, J. Chem. Soc. Chem. Commun. 1978, 1069
55. M. P. Doyle, W. Hu, I. M. Phillips, Org. Lett. 2000, 2, 1777
56. G.-Y. Li, C.-M. Che, Org. Lett. 2004, 6, 1621.
57. J. R. Fulton, V. K. Aggarwal, J. de Vicente, Eur. J. Org. Chem. 2005, 1479.
58. J. Barluenga, C. Valdés, Angew. Chem. 2011, 123, 7626
59. Angew. Chem. Int. Ed. 2011, 50, 7486
60. Z. Shao, H. Zhang, Chem. Soc. Rev. 2012, 41, 560.
61. J. Barluenga, P. Moriel, C. Valdés, F. Aznar, Angew. Chem. 2007, 119, 5683
62. Angew. Chem. Int. Ed. 2007, 46, 5587
63. J. Barluenga, M. Escribano, F. Aznar, C. Valdes, Angew. Chem. 2010, 122, 7008
64. Angew. Chem. Int. Ed. 2010, 49, 6856
65. Q. Xiao, Y. Xia, H. Li, Y. Zhang, J. Wang, Angew. Chem. 2011, 123, 1146
66. Angew. Chem. Int. Ed. 2011, 50, 1114
67. L. Zhou, Y. Shi, Q. Xiao, Y. Liu, F. Ye, Y. Zhang, J. Wang, Org. Lett. 2011, 13, 968
68. X. Zhao, G. Wu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 3296
69. Z.-S. Chen, X.-H. Duan, L.-Y. Wu, S. Ali, K.-G. Ji, P.-X. Zhou, X.-Y. Liu, Y.-M. Liang, Chem. Eur. J. 2011, 17, 6918.
70. Jung and Hagiwara have reported the phenanthrene synthesis by thermal or copper-mediated reaction of dilithium or disodium salts of bistosylhydrazones. See:, M. J. Jung, A. Hagiwara, Tetrahedron Lett. 1991, 32, 3025.
71. G. C. Fu, Acc. Chem. Res. 2008, 41, 1555
72. S. Lou, G. C. Fu, Adv. Synth. Catal. 2010, 352, 2081.
73. S. Kotha, V. R. Shah, K. Mandal, Adv. Synth. Catal. 2007, 349, 1159.
74. For recently review, see:, Y. Shen, C.-F. Chen, Chem. Rev. 2012, 112, 1463.
75. H. Okamoto, N. Kawasaki, Y. Kaji, Y. Kubozono, A. Fujiwara, M. Yamaji, J. Am. Chem. Soc. 2008, 130, 10470
76. R. Mitsuhashi, Y. Suzuki, Y. Yamanari, H. Mitamura, T. Kambe, N. Ikeda, H. Okamoto, A. Fujiwara, M. Yamaji, N. Kawasaki, Y. Maniwa, Y. Kubozono, Nature 2010, 464, 76
77. H. Okamoto, M. Yamaji, S. Gohda, Y. Kubozono, N. Komura, K. Sato, H. Sugino, K. Satake, Org. Lett. 2011, 13, 2758.
78. For a review, see:, H.-J. Knölker, K. R. Reddy, Chem. Rev. 2002, 102, 4303.
79. W. Fröhner, M. P. Krahl, K. R. Reddy, H.-J. Knölker, Heterocycles 2004, 63, 2393 and references therein.